Triethylamine → (2-Chloro-4-methyl-5-nitrophenyl)methanol

Temperatur

0 °C

To a solution of 2-chloro-4-methyl-5-nitrobenzoic acid (CAS; 101580-96-5, 15 g, 69.6 mmol) and triethylamine (11.1 mL, 80 mmol) in THF (200 mL) was added 1,1,1-trichloro-2-methylpropan-2-yl carbonochloridate (19.2 g, 80 mmol) at 0° C., and then the mixture was stirred at 0° C. for 1 hr. The resulting white solid was filtered off through Celite®. The solid was washed by THF (20 mL). To the filtrate was added NaBH4 (3.2 g, 83 mmol) at 0° C., followed by H2O (50 mL). The mixture was stirred at 0° C. for 0.5 h, and then stirred at room temperature for 1.25 h. The reaction was quenched by half satd. KHSO4. The layers were separated and the aqueous layer was extracted with CH2Cl2. The organic layers were combined, washed with H2O and brine, dried over Na2SO4, and then filtered through a silica pad. The SiO2 cake was washed with EtOAc. The residue was concentrated and then triturated with heptane. The resulting solid was collected by filtration to give the title compound. 1H NMR (400 MHz, ACETONITRILE-d3) δ 8.11 (s, 1H), 7.47 (s, 1H), 4.68 (s, 2H), 2.53 (s, 3H).

1. filtrationThe resulting white solid was filtered off through Celite®
2. washThe solid was washed by THF (20 mL)
3. stirringThe mixture was stirred at 0° C. for 0.5 h
4. stirringstirred at room temperature for 1.25 h
5. customThe reaction was quenched by half satd
6. customThe layers were separated
7. extractionthe aqueous layer was extracted with CH2Cl2
8. washwashed with H2O and brine
9. dry with materialdried over Na2SO4
10. filtrationfiltered through a silica pad
11. washThe SiO2 cake was washed with EtOAc
12. concentrationThe residue was concentrated
13. customtriturated with heptane
14. filtrationThe resulting solid was collected by filtration

ORD-Eintrag

ord-6a02f6817eba4b78b608d372f0cef642

Quelldatensatz

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09056874B2